Thionyl Chloride → HCID 9797346, compound

HRID 361313Notes

Reaction equation

HRID 361313 reaction equation
[CH2:1]([C@H:4]1[C@:21]2(O)[C@:16]([CH3:24])([CH2:17][CH2:18][C:19](=[O:23])[CH2:20]2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:25])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3].S(Cl)(Cl)=O>N1C=CC=CC=1>[CH2:1]([C@H:4]1[C:21]2[C@:16]([CH3:24])([CH2:17][CH2:18][C:19](=[O:23])[CH:20]=2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:25])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10854804HCID 10854804, compound

Product 1

HCID 9797346HCID 9797346, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6β-Propargyl-5α-hydroxyandrostane-3,17-dione (10) (0.3 mmol) was dissolved in dry pyridine (10 ml), cooled in an ice-bath and thionyl chloride was added. After stirring for 3-5 minutes, the reaction mixture was poured over ice-water, extracted with ethyl acetate, washed (water), dried, and evaporated in vacuo. The residue was subjected to column chromatography (hexane/ethyl acetate). Recrystallization from acetone/hexane gave the title compound (60% of the analytical product); m.p. 159°-160° C.; IR (KBr) 3245, 2120, 1734, and 1662 (C=O) cm-1 ; 1H-NMR (CDCl3) δ 0.93 (s, 3H, 18-CH3), 1.26 (s, 3H, 19-CH3), 2.6-2.8 (m, 1H), 5.84 (s, 1H, 4-H).

Workup

  1. temperaturecooled in an ice-bath
  2. extractionextracted with ethyl acetate
  3. washwashed (water)
  4. customdried
  5. customevaporated in vacuo
  6. customRecrystallization from acetone/hexane

Sources & evidence

ORD record
ord-19af06684277429bb9753a836394ed41
Source dataset
uspto-grants-1999_02
Patent number
US05866558

Reaction notes

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